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Maximizing the value of a leadership development program - Part 3 of 3: Preparing for and gaining value from coaching

Maximizing the value of a leadership development program - Part 3 of 3: Preparing for and gaining value from coaching
I often think about coaching as a partnership, involving walking side by side with the leader I'm working with, on a long, difficult, but meaningful journey.

This is the third of three articles designed to support leaders in maximizing the value they receive from participating in a leadership development program.

Leadership development programs can take many forms, but one common version involves three key phases: 1) collecting and debriefing in-depth assessment data, 2) building a goal document called a development plan (often informed by the assessment results), and 3) working with a coach to make as much progress against that plan as possible.

In this article, I offer suggestions on how leaders can prepare themselves for, and gain the most value from a coaching engagement within a broader leadership development program.

1. Think about the word 'coach' in a different way

Although the word ‘coach’ is common in our vernacular, its meaning in an executive training setting may differ from the way we typically interpret it. In this section I suggest that it may help leaders to clarify these differences before starting a coaching process.

For example, one of the colloquial ways we use the word ‘coach’ references athletic coaches. However, sports coaching differs from executive coaches in a number of ways. For example, athletic coaches are often highly directive, shaping the strategies of their teams and the actions of their players. By contrast, in executive coaching engagements, leaders (not coaches) direct the proceedings, often choosing the goals to pursue, and the specific topics to discuss.

Sports coaches can also engage in demonstrative behaviour designed to attract attention (e.g., yelling at their own team or officials). In an executive development context, however, coaches spend most of their time listening. They may shy away from bringing attention to themselves and prefer to keep the focus of the discussion on the leader and their chosen topic.

On February 23, 1985, Bobby Knight the head coach of the Inidiana University basketball team, threw a chair onto the court during a game against Purdue University. These kinds of demonstrative behaviours by athletic coaches may contribute to confusion about the role of an executive coach.

The word ‘coaching’ is an imperfect term for the process I’ll describe in this article. Perhaps a more accurate word is ‘partnership.’ The leader and the coach should feel that they’re working together in the interest of addressing the leader’s needs.

In that same vein, another image I gravitate to is the idea of ‘walking with the leader,’ as if side by side. This is a helpful mental model because it suggests a) aligning with and moving at the same pace as the leader, b) going on a long journey together which mirrors the development journey, and c) providing support, comfort, and guidance on this arduous and uncertain path.

Before starting an engagement, leaders might consider discussing with their coach what their relationship involves, and what makes it unique.

2. Take ownership of the process where you feel comfortable

Executive coaches are often the experts on the development process, but leaders need to play a significant role in defining the content of the coaching conversations.

The coach will look to the leader for cues on what they want, need, or prefer to discuss, despite the fact that the leader may perceive the coach as the expert and may want to defer to them.

It may help leaders to come to each coaching session with 2-3 ideas of what they want to discuss.

If leaders are too busy in advance of the meeting to prepare, most coaches will arrive with a ‘shadow’ agenda in the background that they can propose if needed.

Coaching tends to work best when leaders sweat and struggle in their quest to improve. One person I worked with once described a dark side of coaching, which they termed ‘corporate parenting.’ We didn’t unpack the implied meaning at the time, but I assume they were referring to how in some cases leaders might show too much deference to the coach.

It’s helpful for leaders to remember that they have great influence during the coaching process, and that while the coach can advise on procedural steps, they can shape the content and focus of the conversations.

3. The paradox of structure

Although coaching is a fluid, flexible, and non-linear process, one of its paradoxes is that creating some structure in the background helps it unfold smoothly.

One kind of structural support involves steps preceding the coaching. For example, the leadership development process I’ve described in this series of articles involves three phases, a) assessment and feedback, b) development planning, and c) coaching. In this approach, the first two steps create valuable inputs for coaching, like increased receptivity to change, a sense of momentum, and a development plan containing clear goals and actions that can guide the coaching conversations.

Another kind of structure is internal to the coaching engagement, and involves establishing key rules and procedures. One version of this internal structure includes outlining and communicating all the steps in the engagement, such that the leader and the coach know their roles, and the effort and deliverables required (e.g., how many sessions, how frequently, if there will be review meetings with other stakeholders). Leaders should ensure they have clarity on this structure before starting.

Another version of internal structure involves outlining how information will be kept private. I lay out these principles in a ‘Confidentiality Policy’ that I share with the leader at the start of the engagement (i.e., before the assessment). For coaching in particular, some important rules of thumb might be a) that the coach doesn’t share any details of the coaching discussions with anyone else, b) that the coach keeps coaching conversations private in perpetuity after the end of the engagement, and c) that the coach will not hold one-on-one meetings with any other members of the organization without the client present.

The structural features of the engagement should be established in advance (although they can be renegotiated at any point as long as all key parties agree). If the structure of the program doesn’t make sense or work for a leader, they should ask the coach about it. In a strange irony, putting these structural features in place creates more freedom and safety for the leader and coach to explore topics during their sessions.

4. Coaching sessions are like verbal journaling

One source of value for leaders going through coaching is that they get the chance to organize sometimes disparate thoughts during the coaching conversations.

This process is akin to a verbal version of journaling. In a written journal, someone might capture various thought fragments, not understanding if or how they relate. Once that person reviews those thoughts on a physical page, however, they can begin to detect patterns and priorities.

Coaching conversations work in a similar way. In fact leaders often comment to me at the end of a session that they valued the chance to say what was on their mind, hear me reflect a summary back to them (i.e., as if they were reading their written ideas on the page), and then have the chance to organize those thoughts into a cohesive assessment of the situation and action plan.

Sometimes clients find it hard to sense the patterns as they verbalize their thinking. Many leaders even apologize, because they think they’re ‘not making sense.’ If you find yourself speaking in a non-linear way during the coaching sessions, rest assured this is part of the process. Listening to your coach summarize your statements back to you should give you the chance to see a useful constellation of related ideas.

5. What do leaders talk about during coaching sessions?

At the start of coaching processes, sometimes executives ask me ‘what do we talk about in the meetings?’ The short answer is that the leader can choose the topics they’d like to discuss. The longer answer is that coaching conversations can revolve around any of the following areas:

Development plan: A common jumping off point for coaching conversations is the development plan. Leaders may want to use the plan as a kind of agenda for the coaching discussion, working through a recap of progress or difficulties related to pursuing the goals.

Reviewing impediments: When leaders share problems they experience in striving to reach their goals, this often initiates deeper discussions about what causes these impediments. Leaders and coaches can then explore a range of theories explaining those difficulties, problem-solve ways to address them, and then create a revised plan of action.

Planning or reviewing behavioural experiments: Sometimes a leader tries out a new behaviour in between coaching sessions. If so, part of the next meeting can be used to debrief how this experiment unfolded, what was learned, and what new behaviour the leader might want to test in the next experiment.

Principles of leadership/management: Some leaders want to discuss foundational best-practices of leadership and management, and so the coach may share their knowledge of a related topic or skill, based on experience or research.

Discussing other training opportunities/priorities: At some point, leaders may realize they need to seek additional training on a specialized topic. Some of the coaching discussion could be spent identifying the topic they need refinement on, and avenues for seeking that training.

Specific situations the leader faces: Leaders may encounter ‘fresh’ or ‘live’ challenges unrelated to their development goals, which they want to problem-solve with their coach. For example, a leader might say ‘XYZ happened last week, and I’m really struggling to resolve it.’ In these cases, leaders and coaches can spend time in the session assessing the issue at play, and developing a strategy to address it.

Career direction: Questions about a leader’s career direction should arise early in the engagement (e.g., during the intake process, during the background interview, during the goal setting phase), but at times it makes sense to continue pursuing career questions during the coaching phase (e.g., when a leader creates a goal and actions related to advancement).

Meta discussions about the process: Sometimes it’s helpful for leaders and coaches to discuss how the overall process is working (or not) for them. This is important to ensure the relationship between leader and coach remains strong (see the next section for more on this theme). The leader might say to the coach ‘I feel like we’re going around in circles and not making progress.’ As a result, the two might agree on taking some small, achievable actions so the leader can generate a feeling of forward momentum. Or the coach might say ‘I gave you some feedback at the end of the last session, and you said you appreciated it, but I wondered if you felt frustrated by it.’ The two could then discuss reactions to the feedback, clear up any misunderstandings, and repair the relationship if needed.

6. The alliance is everything

Feeling a strong bond, partnership, or alliance with the coach you’re working with is a critical success factor for coaching engagements.

As a thought experiment, how would you feel if a stranger approached you and gave you some advice? How likely would it be for you to act on that advice? Next, imagine your best friend of 20 years giving you that same advice. How would your reaction differ?

One of the most important things a coach will do at the outset of an engagement is build a strong rapport with the leader they’re working with. Some of this will happen naturally as a result of collaborating in several early-stage meetings to launch the leadership development process.

Once the leader and the coach establish a strong bond, many new avenues open up. The leader will become more receptive to feedback or suggestions from the coach. The coach will also feel more comfortable giving honest and direct suggestions to the leader, without fear of offending. The leader’s belief in the value of the process will also increase, and they will become more likely to act on ideas emerging during the conversations.

In the rare case that the alliance isn’t working, great coaches will broach this subject ASAP. However, if leaders sense their alignment with the coach wavering during the process, they should raise their concerns with the coach. Many times misunderstandings can be clarified and the partnership can resume.

7. You can ask the coach what they believe

Sometimes coaches develop a style, or even a philosophy that guides their approach, and it can be informative for leaders to ask about this early in the engagement.

For example, one of my philosophies about coaching involves trying to honour the agency of the leader. This manifests in several ways, like spending most of my time paraphrasing the client’s statements and asking questions, rather than giving suggestions. When I give suggestions, I ask for permission first. The principle of agency also shapes my reluctance to assign homework. I might suggest it, but not assign it, since it’s important for me to respect the leader’s freedom to choose how they develop.

Not every coach possesses a guiding philosophy or set of orienting principles, but many do, and asking about this may help a leader familiarize themselves with the coach’s working style.

8. 'Hello ambivalence, my old friend…’

‘One part of me says this, another says that.’ ‘I’m on the fence.’ ‘On second thought…’ Each of these phrases captures the feelings of ambivalence people often feel when considering a course of action. Ambivalence is also a typical experience of leaders going through any kind of development program, including coaching.

The title of Maile Meloy's 2009 compilation of short stories encapsulates another way in which people often experience ambivalence. 

When contemplating behaviour change, leaders often toggle between different modes of thinking, which can include: a) being vaguely aware of the possibility of change, but in a less conscious way, b) being fully aware of wanting to change, c) starting to make plans to change but not yet acting, and d) being aware of the need to change, creating plans, and acting in ways that create that change.

Before entering into a coaching process, leaders should realize that ambivalence about change is normal. People move through each of the above stages many times, in a circuitous way, forwards and backwards, forwards and backwards again, before gaining traction on a goal to change. Outside of coaching engagements, it’s common for people to stay perched on the fence, unsure about whether to change for years! So I want to destigmatize ambivalence, and help leaders understand that it is 100% normal. In fact, who among us would change a long-held behaviour pattern in an instant, without some serious reservation? If you did, many would consider you misguided or worse.

The leadership development and coaching processes should help leaders work through their feelings of reluctance in a productive way. The feedback stage creates a strong case for change, based on consensus themes emerging from the assessment. And the coaching process provides a forum to explore ambivalence. An effective coach will slow down the process at the first sign of ambivalence, and help the leader explore all the angles associated with conflicting feelings.

Regardless of the nature of the ambivalence, leaders should understand that these feelings are typical when considering behaviour change, and should recognize that the coaching sessions are an ideal forum for exploring those feelings.


The purpose of this article was to provide suggestions on how leaders can prepare themselves for, and gain the most value from a coaching engagement inside a leadership development program.

I hope this article provided a useful orientation about what a coaching engagement involves and how it could unfold.

I also hope the previous two articles in this series gave you helpful insights as you prepare to participate in a leadership development program, or strive to extract the most value from one you’re already a part of. I wish all of you well in your journey to further strengthen your leadership effectiveness.

As always I would welcome your feedback, positive or constructive, on any of these points, and would love to learn from your unique perspective.

Starting in two weeks, I’ll begin publishing a longer series of articles describing key lessons I’ve learned from both academic and practitioner settings, on what either drives or derails effective leadership.

I hope you’ll continue to read, and if you’d like to receive these newsletter issues direct to your email, please sign up by clicking on the blue ‘Sign up now’ button below.

Tim Jackson Ph.D. is the President of Jackson Leadership, Inc. and a leadership assessment and coaching expert with 17 years of experience. He has assessed and coached leaders across a variety of sectors including agriculture, chemicals, consumer products, finance, logistics, manufacturing, media, not-for-profit, pharmaceuticals, healthcare, and utilities and power generation, including multiple private-equity-owned businesses. He's also worked with leaders across numerous functional areas, including sales, marketing, supply chain, finance, information technology, operations, sustainability, charitable, general management, health and safety, and quality control, and across hierarchical levels from individual contributors to CEOs. In addition Tim has worked with leaders across several geographical regions, including Canada, the US, Western Europe, and China. He has published his ideas on leadership in both popular media, and peer-reviewed journals. Tim has a Ph.D. in organizational psychology, and is based in Toronto.

Web: www.jacksonleadership.com

Email: tjackson@jacksonleadership.com